Hydroxyamine hydrochloride → HCID 85521050, compound

HRID 2301942Notes

Reaction equation

HRID 2301942 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[OH:18][NH2:19].C([O-])(=O)C.[Na+].C(OCC)(=O)C.CCCCCC>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[N:19][OH:18])[CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 135552471-(3,4-Dimethoxyphenyl)pentan-1-oneHCID 21226206Ethyl acetate hexane

Product 1

HCID 85521050HCID 85521050, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 3′,4′-dimethoxyvalerophenone (0.08 grams, 3.60 mmol) in a mixture of ethanol (25 milliliters) and water (5 milliliters) was added hydroxyamine hydrochloride (0.40 grams, 5.76 mmol) and sodium acetate (0.59 grams, 7.20 mmol) in water (5 milliliters). The solution was refluxed for two days. Reaction progress was monitored by TLC (20%, ethyl acetate/hexane, UV) and was complete after 2 days. The reaction was allowed to cool to ambient temperature and the ethanol was removed in vacuo to afford an oil/aqueous mixture. The mixture was extracted with methylene chloride. The dried extracts were concentrated in vacuo to afford 0.93 grams of crude product as a yellow oil. The crude product was purified by flash chromatography (silica gel, 20%, ethyl acetate/hexane) to afford 0.56 grams of product as a yellow oil: 1H NMR (CDCl3) δ8.23-8.01(br s, 1H), 7.30-7.05(m, 2H), 6.93-6.81(m, 1H), 3.91(s, 3H), 3.90(s, 3H), 2.84-2.70(m, 2H), 1.74-1.31(m, 4H), 0.93(t, J=7.2 Hz, 3H);13 C NMR (CDCl3) δ159.6, 150.1, 148.9, 128.5, 119.3, 110.6, 108.9, 55.9, 28.7, 25.6, 22.9, 13.8.

Workup

  1. temperatureThe solution was refluxed for two days
  2. customReaction progress
  3. customthe ethanol was removed in vacuo
  4. customto afford an oil/aqueous mixture
  5. extractionThe mixture was extracted with methylene chloride
  6. concentrationThe dried extracts were concentrated in vacuo
  7. customto afford 0.93 grams of crude product as a yellow oil
  8. customThe crude product was purified by flash chromatography (silica gel, 20%, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a8ca7c3e4c2c48c18d0f4dbdb4d6376d
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

Loading…